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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2008-12-10 02:07:10 UTC |
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Update Date | 2020-02-26 21:34:51 UTC |
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HMDB ID | HMDB0011300 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PC(P-18:1(11Z)/P-18:1(11Z)) |
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Description | PC(P-18:1(11Z)/P-18:1(11Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(P-18:1(11Z)/P-18:1(11Z)), in particular, consists of two chains of plasmalogen 18:1n7 at the C-1 and C-2 positions. The plasmalogen 18:1n7 moieties are derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. |
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Structure | |
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Synonyms | Value | Source |
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(2R)-2,3-Bis[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propyl 2-(trimethylazaniumyl)ethyl phosphoric acid | Generator, HMDB |
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Chemical Formula | C44H84NO6P |
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Average Molecular Weight | 754.131 |
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Monoisotopic Molecular Weight | 753.603626427 |
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IUPAC Name | (2R)-2,3-bis[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propyl 2-(trimethylazaniumyl)ethyl phosphate |
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Traditional Name | (2R)-2,3-bis[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propyl 2-(trimethylammonio)ethyl phosphate |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](CO\C=C/CCCCCCCC\C=C/CCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)O\C=C/CCCCCCCC\C=C/CCCCCC |
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InChI Identifier | InChI=1S/C44H84NO6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-39-48-42-44(43-51-52(46,47)50-41-38-45(3,4)5)49-40-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h16-19,36-37,39-40,44H,6-15,20-35,38,41-43H2,1-5H3/b18-16-,19-17-,39-36-,40-37-/t44-/m1/s1 |
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InChI Key | LTQBTADUGKSCOZ-WRCNLVTNSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Glycerophospholipids |
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Sub Class | Glycerophosphocholines |
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Direct Parent | Glycerophosphocholines |
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Alternative Parents | |
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Substituents | - Glycero-3-phosphocholine
- Phosphocholine
- Glycerol vinyl ether
- Dialkyl phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Quaternary ammonium salt
- Tetraalkylammonium salt
- Amine
- Organic salt
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-9120232300-19053aae13a84480bd5d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052k-9373274000-b09a290fa630b2076c0f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-007a-9062153000-c89ef35164d9ced46b1d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0060003900-e74a999b3e619fc0559c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-1090206100-4cc859ff8fe827154e72 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-016r-5191500000-e161eba351c917d962ed | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 44.5 (37.6-53.3) uM | Newborn (0-30 days old) | Not Available | Normal | | details | Blood | Detected and Quantified | 267.03(66.1) uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 212 (183-244) uM | Infant (0-1 year old) | Not Available | Normal | | details | Blood | Detected and Quantified | 250.7 +/- 47.2 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 0.84 +/- 2 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 1.46 +/- 2.13 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 0.200 +/- 0.031 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.016 (0.0021-0.045) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 220.75(59.14) uM | Adult (>18 years old) | Both | Heart failure with preserved ejection fraction | | details | Blood | Detected and Quantified | 192.7 +/- 50.0 uM | Children (1-13 years old) | Both | Obesity | | details | Blood | Detected and Quantified | 233.6 +/- 68.4 uM | Children (1-13 years old) | Both | Obesity | | details | Blood | Detected and Quantified | 155.673 (140.706) uM | Adult (>18 years old) | Female | Pregnancy with fetus having congenital heart defect | | details | Blood | Detected and Quantified | 279.018 (74.520) uM | Adult (>18 years old) | Female | Pregnancy | | details | Feces | Detected but not Quantified | Not Quantified | Newborn (0-30 days old) | Not Specified | Premature neonates | | details | Feces | Detected but not Quantified | Not Quantified | Newborn (0-30 days old) | Not Specified | Premature neonates | | details |
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Predicted Concentrations |
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Blood | 0.000 +/- 0.000 uM | Adult (>18 years old) | Both | Normal (Most Probable) | Calculated using MetaboAnalyst | Blood | 0.417 +/- 0.161 uM | Adult (>18 years old) | Both | Normal (Upper Limit) | Calculated using MetaboAnalyst |
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Associated Disorders and Diseases |
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Disease References | Pregnancy |
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- Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
| Obesity |
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- Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 131801673 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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